Alkylidine aminooxyamide compounds useful in controlling undesirable vegetation

ABSTRACT

Compounds having the formula ##STR1## wherein R is C 1  -C 6  lower alkoxy; C 1  -C 6  lower alkylthio; 3- to 6-membered heterocycle or substituted heterocycle; phenyl or substituted phenyl; R 1  is hydrogen or C 1  -C 3  lower alkyl; R 2  is selected from the group consisting of hydrogen, C 1  -C 3  lower alkyl, C 3  -C 6  cycloalkyl, C 1  -C 3  lower alkylalkoxy or combinations thereof; R 3  and R 4  are independently selected from the group consisting of hydrogen; C 1  -C 6  lower alkyl; C 2  -C 6  lower alkenyl; C 2  -C 6  lower alkynyl; 3- to 6-membered heterocyle or substituted heterocycle; alkyl heterocycle or substituted alkyl heterocycle; phenyl or substituted phenyl; and where R 3  l or R 4  is a basic heterocyle, herbicidally acceptable organic or inorganic salts thereof are herbicidally active.

Background of the Invention

This invention relates to herbicides and, more particularly, to certainnovel substituted alkylidine aminooxyamides.

Certain aminooxy alkanoic acids and esters having the formula ##STR2##wherein X is halogen, OM in which M is an alkali metal, an alkalineearth metal, silver or ammonium cation, OH or OR₃ in which R₃ is analkyl or alkoxyalkyl group containing from 1-10 carbon atoms;

R is an alkyl group containing from 2 to 4 carbon atoms;

R₁ is a hydrogen atom or an alkyl group containing from 1 to 6 carbonatoms, optionally substituted by one or more halogen atoms; and

R₂ is an alkyl or alkenyl group containing from 1 to 6 carbon atoms, aphenyl group optionally substituted by one or more substituents selectedfrom a halogen atom, a nitro group, an alkyl, alkylthio or alkoxy groupcontaining from 1 to 4 carbon atoms, each optionally substituted by oneor more halogen atoms, or by a methylenedioxy group; or

R₁ and R₂ taken together with the carbon atom to which they are attachedform a cyclic hydrocarbyl group containing from 3 to 12 carbon atoms,have been found to be useful as herbicides and plant growth regulatorsare taught in EPO 182,407, issued to Sanborn et al.

The novel compounds of our invention have been found to be activeherbicides possessing herbicidal activity against various species ofweeds In the broadest sense, the term "weeds" refers to plants whichgrow in locations in which they are not desired.

Our invention therefore also relates to a method for controllingundesirable vegetation, comprising applying to a locus where control ofsuch vegetation is desired an herbicidally effective amount of acompound as described herein, and also relates to herbicidalcompositions of matter comprising an herbicidally effective amount of acompound as described herein, together with an inert diluent or carriersuitable for use with herbicides.

As used herein the term "herbicide" refers to compounds which adverselycontrol or modify the growth of plants, particularly of undesirableplants. By the term "herbicidally effective amount" is meant an amountof compound which causes an adverse controlling or modifying effect onthe growth of plants. The term "plants" is meant to include germinantseeds, emerging seedlings, and established vegetation, including rootsand above-ground portions. Such adverse modifying and controllingeffects may include all deviations from natural development.

Included with this invention is the composition of matter and method ofuse.

BRIEF DESCRIPTION OF THE INVENTION

This invention relates to novel herbicidal compounds having the formula##STR3## wherein R is lower alkoxy; lower alkylthio; heterocycle suchas, but not limited to, thiazole, thiazole substituted with one or morelower alkyl, halo or lower haloalkyl, thiadiazole, thiadiazolesubstituted with one or more lower alkyl, halo or lower haloalkyl,thienyl, thienyl substituted with one or more lower alkyl, halo or lowerhaloalkyl, pyridyl, pyridyl substituted with one or more lower alkyl orhalo; phenyl or phenyl substituted with one or more lower alkyl, loweralkoxy, halo, lower haloalkyl, lower haloalkoxy, cyano, nitro, phenoxy,pyridyloxy, lower alkylsulfonyl or combinations thereof;

R₁ is hydrogen or lower alkyl;

R₂ is selected from the group consisting of hydrogen, lower alkyl, lowercycloalkyl, lower alkylalkoxy or combinations thereof;

R₃ and R₄ are independently selected from the group consisting ofhydrogen; lower alkyl; lower alkenyl; lower alkynyl; pyridyl or pyridylsubstituted with one or more halogen or lower alkyl; lower alkylpyridylor lower alkylpyridyl substituted with one or more halogen or loweralkyl; phenyl or phenyl substituted with one or more lower alkyl, loweralkoxy, halo, lower haloalkyl, lower haloalkoxy, nitro, lower alkylthio,lower alkylsulfonyl or combinations thereof; benzyl, alpha-lower alkylsubstituted benzyl, or benzyl substituted with one or more lower alkyl,halo, lower haloalkyl, or combinations thereof; thienyl, thienylsubstituted with one or more lower alkyl or halo; piperonyl, furfuryl ormethyl naphthyl; or when R₃ or R₄ are pyridyl, herbicidally acceptableorganic or inorganic salts thereof.

DETAILED DESCRIPTION OF THE INVENTION

This invention relates to novel herbicidal compounds having the formula##STR4## wherein R is lower alkoxy; lower alkylthio; heterocycle suchas, but not limited to, thiazole, thiazole substituted with one or morelower alkyl, halo or lower haloalkyl, thiadiazole, thiadiazolesubstituted with one or more lower alkyl, halo or lower haloalkyl,thienyl, thienyl substituted with one or more lower alkyl, halo or lowerhaloalkyl, pyridyl, pyridyl substituted with one or more lower alkyl orhalo, phenyl; or phenyl substituted with one or more lower alkyl, loweralkoxy, halo, lower haloalkyl, lower haloalkoxy, cyano, nitro, phenoxy,pyridyloxy, lower alkylsulfonyl or combinations thereof;

R₁ is hydrogen or lower alkyl;

R₂ is selected from the group consisting of hydrogen, lower alkyl, lowercycloalkyl, lower alkylalkoxy or combinations thereof;

R₃ and R₄ are independently selected from the group consisting ofhydrogen; lower alkyl; lower alkenyl; lower alkynyl; pyridyl or pyridylsubstituted with one or more halogen or lower alkyl; lower alkylpyridylor lower alkylpyridyl substituted with one or more halogen or loweralkyl; phenyl or phenyl substituted with one or more lower alkyl, loweralkoxy, halo, lower haloalkyl, lower haloalkoxy, nitro, lower alkylthio,lower alkysulfonyl or combinations thereof; benzyl, alpha-lower alkylsubstituted benzyl, or benzyl substituted with one or more lower alkyl,halo, lower haloalkyl, or combinations thereof; thienyl, thienylsubstituted with one or more lower alkyl or halo; piperonyl, furfuryl ormethyl naphthyl; or when R₃ or R₄ are pyridyl, herbicidally acceptableorganic or inorganic salts thereof.

The compounds of this invention can be prepared via standard methods,including the methods as shown in the following Schemes I-X.

The desired oxime can be reacted at 30°-150° C. in a suitable solventsuch as dimethylformamide (DMF) with the desired ester as shown in thefollowing Scheme I: ##STR5## wherein R and R₂ are as defined above whichis then hydrolyzed at 20°-50° C. in the presence of a base such assodium hydroxide followed by acidification as shown in the followingScheme II: ##STR6## The resulting acid is then converted to the acidchloride at 40°-80° C. in a solvent such as toluene with phosgene andusing DMF as a catalyst to produce the chloride as shown in thefollowing Scheme III: ##STR7## Said acid chloride can then be reactedwith an amine at 20°-40° C. as shown in the following Scheme IV:##STR8## wherein R₃ and R₄ are as defined above. The acid of the desiredoxime can also be reacted with the amine of choice at 20°-30° C. in thepresence of carbonyldiimidazole as shown in the following Scheme V:##STR9## N-Hydroxy phthalimide can be reacted with the desired haloamideat 50°-100° C. in a suitable solvent such as dimethylformamide in thepresence of a metal hydride (MH) as shown in the following Scheme VI:##STR10## wherein R₂, R₃, and R₅ are as defined as above, provided thatwhen R₄ is phenyl or pyridyl, R₃ is other than hydrogen, which is thenfollowed by reaction with a hydrazine at 20°-40° C. as shown in thefollowing Scheme VII: ##STR11## and then reacted with an aldehyde asshown in the following Scheme VIII: ##STR12## wherein X is one or morealkyl, alkoxy, halo, haloalkyl, cyano, hydroxy, nitro, phenoxy orcombinations thereof, or, alternatively, the desired benzaldehyde oximecan be reacted with the desired haloamide at 40°-100° C. in a suitablesolvent such as dimethylformamide in the presence of a base such aspotassium carbonate as shown in the following Scheme IX: ##STR13##wherein R₃ and R₄ are as defined in Scheme VI above. The oxime whereinR₄ is a basic heterocycle such as pyridyl can be reacted with an organicor inorganic acid at 0°-40° C. in the presence of a suitable solvent toproduce the corresponding salt as shown in scheme X. ##STR14##

The term "lower alkyl" includes moieties having from about 1 to about 6carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, isobutyl and tert-butyl, as well as the six pentyls andsixteen hexyls.

The term "lower alkenyl" includes moieties having from about 2 to about5 carbon atoms such as ethenyl, propenyl, isopropenyl, butenyl,isobutenyl, pentenyl, sec-pentenyl and isopentenyl.

The term "lower alkynyl" includes moieties having from about 2 to about5 carbon atoms such as ethynyl, propynyl, butynyl, pentynyl andisopentynyl.

The term "lower cycloalkyl" includes unsaturated cyclic moieties havingfrom about 3 to about 6 carbon atoms such as cyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl.

The term "lower alkoxy" includes both straight and branched chainacyclic hydrocarbyl moieties which contain an oxygen in the chain andincludes such moieties having from about 1 to about 4 carbon atoms, forexample, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, secbutoxy,isobutoxy and tert-butoxy.

The term "halo" includes fluorine, chlorine, bromine or iodine as mono-,di-, tri- and mixed halogen substitutions.

By "heterocycle" is meant a 3- to 6-membered ring compound in which atleast one member in the ring is other than carbon such as but notlimited to thiazole or thiazole substituted with one or more C₁ -C₃lower alkyl, halo or C₁ -C₃ lower alkyl; thiadiazole or thiadiazolesubstituted with one or more C₁ -C₃ lower alkyl, halo or C₁ -C₃ lowerhaloalkyl; pyridyl or pyridyl substituted with one or more C₁ -C₃ alkyl,halo or C₁ -C₃ lower haloalkyl; thienyl or thienyl substituted with oneor more C₁ -C₃ lower alkyl, halo or C₁ -C₃ lower haloalky or piperonyl.

Pyridylaminooxyamides of the invention are basic. The pyridyl nitrogencan be at the 2-, 3- or 4-position and the unprotonated nitrogen atom ofthe pyridyl ring can be protonated by an acid, either organic orinorganic. Representative inorganic acids are hydrochloric, nitric,hydrobromic, sulfuric, sulfamic and phosphoric. Representative organicacids are acetic, trifluoroacetic, benzoic, benzenesulfonic,p-toluenesulfonic, naphthalenesulfonic, phenylphosphonic andorganophosphonic. The salts so formed are also herbicidal.

The following are examples of the preparation of the compounds of thisinvention, the structures of which were confirmed by spectroscopy. Theseexamples are offered strictly for purposes of illustration and areintended neither to limit nor to define the invention in any manner.

EXAMPLE I Preparation ofMethyl-2-[1-(3-trifluoromethylphenyl)methylene]-aminooxybutyrate (asshown in Scheme I above)

A solution of 80.0 grams (g) (0.42 mols) ofm-trifluoromethylbenzaldoxime in 250 milliliters (ml) ofdimethylformamide was added to a solution of 69.1 g (0.50 mol) potassiumcarbonate in 80 mL of water with rapid stirring. After 15 minutes, 76.6g (0.42 mol) of methyl-2-bromobutyrate was added to the oxime mixtureand this was heated at 80° C. for 2 hours. The mixture was then pouredinto 1 liter of ice water and extracted sequentially with two 150 mLportions of toluene. The combined toluene extracts were shakensequentially with three 150 mL portions of brine, dried and evaporatedto leave a liquid, 112.3 g, b.p. 122°-125° C./1.25 mm identified as thetitle compound by infrared (IR), nuclear magnetic resonance (NMR) andmass spectroscopy (MS).

EXAMPLE II Preparation of2-[1-(3-Trifluoromethylphenyl)methylene]-aminooxybutyric acid (as shownin Scheme II above)

Ethyl-2-[1-(3-trifluoromethylphenyl)methylene]aminooxybutyrate (141 g,0.46 mol) was added to a stirred mixture of 38.4 g (0.48 mol) of 50%aqueous sodium hydroxide, 70 mL water and 425 mL ethanol. The mixturewas refluxed for 3 hours, cooled to room temperature, and evaporatedunder reduced pressure. The residue was taken up in 300 mL water and theresulting mixture was extracted with 150 mL ether. The aqueous layer wasremoved and acidified with concentrated hydrochloric acid solution. Theproduct separated as an oil and it was removed by extraction with 200 mLether. The ether extract was shaken with 100 mL brine, dried over MgSO₄and evaporated to leave an oil, 99.2 g, identified by NMR spectroscopyas the acid.

EXAMPLE III Preparation ofN-(2-Pyridylmethyl)-2-[1-(3-trifluoromethylphenyl)methylene]-aminooxybutyramide(as shown in Scheme V above)

A solution of 4.0 g (15 mmol) of2-[1-(3-trifluoromethylphenyl)methylene]aminooxybutyric acid in 100 mLmethylene chloride was stirred under nitrogen and 2.4 g (15 mmol) ofcarbonyl diimidazole was added to it. Within 15 minutes CO₂ evolutionsubsided and 1.6 g (15 mmol) of 2-(aminomethyl)pyridine were added. Themixture was stirred at room temperature for 3 hours and then allowed tostand overnight. The mixture was next shaken with 100 mL portions ofwater, saturated sodium bicarbonate and brine followed by drying overmagnesium sulfate. Removal of solvent at reduced pressure left an oil,4.1 g, n_(D) ³⁰ 1.5305, identified as the title compound by NMR, MS andIR.

EXAMPLE IV Preparation ofN-(2-Chlorobenzyl)-2-(N'-phthalimidooxy)-butyramide (as shown in SchemeVI above)

A mixture of 0.3 g (14 mmol) sodium hydride in 80 mL of drydimethylformamide was stirred under a blanket of nitrogen and 2.3 g (14mmol) of solid N-hydroxyphthalimide was added to it at 25°-30° C. A deepred color developed. After 0.75 hour 4.0 g (14 mmol) ofN-(2-chlorobenzyl)-2-bromobutyramide was added in one portion and themixture was heated at 100° C. for one hour. During this time the mixturebecame yellow. The mixture was then poured into 200 mL brine andextracted sequentially with two 100 mL portions of toluene. The combinedtoluene extracts were shaken sequentially with three 100 mL portions ofbrine, dried over magnesium sulfate, filtered and evaporated to leave asolid, 4.3 g. The crude product was recrystallized from ethyl alcohol toyield 2.1 g, m.p. 131°-133° C., identified as the title compound by IR,NMR and MS.

EXAMPLE V Preparation of N-(2-Chlorobenzyl)-1-aminooxybutyramide (asshown in Scheme VII above)

Hydrazine hydrate (1.2 g, 22 mmol) was added to a mixture of 4.0 g (11mmol) of N-(o-chlorobenzyl)-2-(N'-phthalimidooxy)butyramide in 100 mlethyl alcohol. There as a slight exotherm and a new solid formed. Themixture was heated at 40° C. for 2 hours and cooled to 5° C. It wasfiltered and the filtrate was evaporated to leave a solid, 2.4 g, m.p.65°-70° C. This was identified as the title compound by IR, NMR and MS.

EXAMPLE VI Preparation ofN-(2-Chlorobenzyl)-2-[1-(3-chlorophenyl)methylene]-aminooxybutyramide(as shown in Scheme VIII above)

A mixture of 2.8 g (12 mmol) of N-(2-chlorobenzyl)-2-aminooxybutyramideand 1.6 g (12 mmol) of 3-chlorobenzaldehyde in 75 mL ethanol was heatedat reflux for 1 hour. The solvent was then removed at reduced pressureand the residue was taken up in 100 mL methylene chloride, washed with50 mL brine and dried over magnesium sulfate. Removal of solvent undervacuum left an oil which crystallized, 3.1 g, m.p. 70°-74° C.,identified as the title compound by NMR, MS and IR.

EXAMPLE VII Preparation ofN-Benzyl-2-[1-(3-trifluoromethylphenyl)methylene]-aminooxybutyramide (asshown in Scheme IX above)

A mixture of 2.5 g (18 mmol) potassium carbonate, 15 mL water and 50 mLdimethylformamide was stirred and 3.0 g (16 mmol) ofm-trifluoromethylbenzaldoxime was added. After 0.5 hour, 4.0 g (16 mmol)of N-benzyl-2-bromobutyramide was added and the mixture was heated at90° C. for 20 hours. It was then cooled and poured into 250 mL water.The separated organic material was removed by extraction with two 100 mLportions of toluene. The combined toluene extracts were shaken withthree 100 mL portions of brine, dried and evaporated under vacuum toleave an oil, 4.5 g. The oil was purified by column chromatography onsilica gel Grade 60 using a solution of 65% hexane, 33% ethylacetate,and 2% acetic acid (v/v/v) as eluent. This gave 2.0 g of a solid, m.p.64°-67° C. identified as the title compound by NMR, MS and IRspectroscopy.

EXAMPLE VIII Preparation of2-(Pyridylmethyl)-2[1-(3-trifluoromethylphenyl)methylene]aminooxybutyramidehydrochloride (as shown in Scheme X above)

4.8 Grams (13 mmol) of2-(pyridylmethyl)-2-[1-(3-trifluorophenyl)methylene]aminooxybutyramidewere dissolved in 100 mL ethanol and 1.6 g (17 mmol) of concentratedhydrochloric acid were added dropwise. The mixture was evaporated underreduced pressure and 50 mL ethanol was added to the resulting oil andagain evaporated to yield 5.4 g of an oil which later crystallized andwas identified as the title compound by IR, NMR, and MS.

The following Table I illustrates embodiments of this invention,together with physical data in the form of melting point ranges orrefractive indices where such measurements were possible and physicaldescriptions of the product where neither melting points nor refractiveindices could be taken. Structures of the indicated compounds wereconfirmed by spectroscopy.

                                      TABLE I                                     __________________________________________________________________________     ##STR15##                                                                                                                        Physical                                                                      Constant                  Cmpd.                                               n.sub.D.sup.30 or         No. R            R.sub.1                                                                            R.sub.2 R.sub.3  R.sub.4      m.p.                      __________________________________________________________________________                                                        °C.                     ##STR16##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR17##   1.5235                    2                                                                                  ##STR18##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H        CH.sub.3     83-86                     3                                                                                  ##STR19##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR20##   1.5119                    4                                                                                  ##STR21##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR22##   1.5305                    5                                                                                  ##STR23##   H    CH.sub.2 CH.sub.3                                                                     H        CH.sub.3     semi- solid               6                                                                                  ##STR24##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR25##   64-67                     7                                                                                  ##STR26##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR27##   50-57                     8                                                                                  ##STR28##   CH.sub.3                                                                           CH.sub.3                                                                              H                                                                                       ##STR29##   72-75                     9                                                                                  ##STR30##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR31##   62-70                     10                                                                                 ##STR32##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR33##   oily solid                11                                                                                 ##STR34##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR35##   1.5612                    12                                                                                 ##STR36##   CH.sub.3                                                                           CH.sub.3                                                                              H                                                                                       ##STR37##   1.5264                    13                                                                                 ##STR38##   CH.sub.3                                                                            ##STR39##                                                                            H                                                                                       ##STR40##   1.5200                    14  CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR41##   1.5085                    15                                                                                 ##STR42##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR43##   1.5640                    16                                                                                 ##STR44##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H        CH.sub.2 CHCH.sub.2                                                                        52-55                     17                                                                                 ##STR45##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR46##   1.5236                    18                                                                                 ##STR47##   C.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR48##   1.5215                    19                                                                                 ##STR49##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR50##   1.5205                    20                                                                                 ##STR51##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H        CH.sub.2 C CH                                                                              53-56                     21                                                                                 ##STR52##   CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                        1.4958                    22                                                                                 ##STR53##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR54##   1.5745                    23                                                                                 ##STR55##   H    CH.sub.3                                                                              H                                                                                       ##STR56##   64-66                     24                                                                                 ##STR57##   H                                                                                   ##STR58##                                                                            H                                                                                       ##STR59##   opaque oil                25                                                                                 ##STR60##   H    CH.sub.2 CH.sub.3                                                                     H        CH.sub.2 CCH glass                     26                                                                                 ##STR61##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR62##   43-48                     27                                                                                 ##STR63##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR64##   105-110                   28  CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR65##   1.5195                    29                                                                                 ##STR66##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR67##   137-140                   30                                                                                 ##STR68##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR69##   1.5425                    31                                                                                 ##STR70##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR71##   1.5370                    32                                                                                 ##STR72##   H    CH.sub.2 CH.sub.2 CH.sub.3                                                            H                                                                                       ##STR73##   oily solid                33                                                                                 ##STR74##   H    CH.sub.2 CH.sub.2 CH.sub.3                                                            H                                                                                       ##STR75##   waxy solid                34                                                                                 ##STR76##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR77##   70-76                     35                                                                                 ##STR78##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR79##   70-74                     36                                                                                 ##STR80##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR81##   1.5161                    37                                                                                 ##STR82##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR83##   65-70                     38                                                                                 ##STR84##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR85##   1.5333                    39                                                                                 ##STR86##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR87##   1.5182                    40                                                                                 ##STR88##   H    CH.sub.2 OCH.sub.3                                                                    H                                                                                       ##STR89##   1.5093                    41                                                                                 ##STR90##   H    CH.sub.2 OCH.sub.3                                                                    H                                                                                       ##STR91##   oily solid                42                                                                                 ##STR92##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR93##   1.5338                    43                                                                                 ##STR94##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR95##   opaque oil                44                                                                                 ##STR96##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR97##   1.5310                    45                                                                                 ##STR98##   H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR99##   1.5410                    46                                                                                 ##STR100##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR101##  65-72                     47  CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                    H                                                                                       ##STR102##  1.5250                    48                                                                                 ##STR103##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR104##  1.5385                    49                                                                                 ##STR105##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR106##  1.5356                    50  CH.sub.3 CH.sub.2 S                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR107##  1.5390                    51                                                                                 ##STR108##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR109##  1.5270                    52  CH.sub.3 CH.sub.2 S                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR110##  viscous oil               53  CH.sub.3 CH.sub.2 S                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR111##  1.5630                    54                                                                                 ##STR112##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR113##  82-90                     55                                                                                 ##STR114##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR115##  1.5305                    56                                                                                 ##STR116##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR117##  1.5348                    57                                                                                 ##STR118##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR119##  semi- solid               58  CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR120##  53-60                     59                                                                                 ##STR121##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR122##  1.5191                    60                                                                                 ##STR123##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR124##  93-100                    61                                                                                 ##STR125##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR126##  63-67                     62                                                                                 ##STR127##  H    CH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                                ##STR128##  1.5398                    63                                                                                 ##STR129##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR130##  1.5162                    64                                                                                 ##STR131##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR132##  95-97                     65                                                                                 ##STR133##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR134##  1.5115                    66                                                                                 ##STR135##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR136##  67-73                     67                                                                                 ##STR137##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR138##  70-75                     68                                                                                 ##STR139##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR140##  1.5195                    69                                                                                 ##STR141##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR142##  1.5185                    70                                                                                 ##STR143##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR144##  oily solid                71                                                                                 ##STR145##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR146##  88-93                     72                                                                                 ##STR147##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR148##  82-85                     73                                                                                 ##STR149##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR150##  oily solid                74                                                                                 ##STR151##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR152##  1.5660                    75                                                                                 ##STR153##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR154##  60-65                     76                                                                                 ##STR155##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR156##  dark oil                  77                                                                                 ##STR157##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR158##  oily solid                78                                                                                 ##STR159##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR160##  67-72                     79                                                                                 ##STR161##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR162##  oily solid                80                                                                                 ##STR163##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR164##  viscous oil               81                                                                                 ##STR165##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR166##  73-85                     82                                                                                 ##STR167##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR168##  52-57                     83                                                                                 ##STR169##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR170##  95-98                     84                                                                                 ##STR171##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR172##  oily solid                85                                                                                 ##STR173##  H    CH.sub.2 CH.sub. 3                                                                    H                                                                                       ##STR174##  oily solid                86                                                                                 ##STR175##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR176##  1.5842                    87                                                                                 ##STR177##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR178##  78-81                     88                                                                                 ##STR179##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR180##  1.5010                    89                                                                                 ##STR181##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR182##  oily solid                90                                                                                 ##STR183##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR184##  53-56                     91                                                                                 ##STR185##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR186##  115-120                   92                                                                                 ##STR187##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR188##  dark oil                  93                                                                                 ##STR189##  H    CH.sub.2 CH.sub.3                                                                     H        CH.sub.2 CH.sub.2                                                                          1.5249                    94                                                                                 ##STR190##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR191##  1.5625                    95                                                                                 ##STR192##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR193##  1.5621                    96                                                                                 ##STR194##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR195##  98-103                    97                                                                                 ##STR196##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR197##  75-80                     98                                                                                 ##STR198##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR199##  100-105                   99                                                                                 ##STR200##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR201##  82-88                     100 CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR202##  68-72                     101 CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR203##  43-46                     102 CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR204##  1.4895                    103 CH.sub.3 CH.sub.2 O                                                                        CH.sub.3                                                                           CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR205##  1.5063                    104                                                                                ##STR206##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR207##  60-63                     105                                                                                ##STR208##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR209##  waxy solid                106                                                                                ##STR210##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR211##  85-88                     107                                                                                ##STR212##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR213##  65-70                     108                                                                                ##STR214##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR215##  68-72                     109                                                                                ##STR216##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR217##  56-59                     110                                                                                ##STR218##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR219##  1.5432                    111                                                                                ##STR220##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR221##  85-87                     112                                                                                ##STR222##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR223##  1.5360                    113                                                                                ##STR224##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR225##  1.5008                    114                                                                                ##STR226##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR227##  1.5295                    115                                                                                ##STR228##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR229##  1.5055                    116                                                                                ##STR230##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR231##  1.5805                    117                                                                                ##STR232##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR233##  1.5282                    118                                                                                ##STR234##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR235##  1.5355                    119                                                                                ##STR236##  H    H       CH.sub.1 CH.sub.3                                                                       ##STR237##  oily solid                120                                                                                ##STR238##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR239##  59-62                     121                                                                                ##STR240##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR241##  1.5338                    122                                                                                ##STR242##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR243##  1.5066                    123                                                                                ##STR244##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR245##  55-60                     124                                                                                ##STR246##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR247##  1.5204                    125                                                                                ##STR248##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR249##  76-78                     126                                                                                ##STR250##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR251##  75-80                     127                                                                                ##STR252##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR253##  80-83                     128                                                                                ##STR254##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR255##  97-100                    129                                                                                ##STR256##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR257##  93-97                     130                                                                                ##STR258##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR259##  92-95                     131                                                                                ##STR260##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR261##  58-62                     132                                                                                ##STR262##  H    H       CH.sub.2 CH.sub.3                                                                       ##STR263##  1.5275                    133                                                                                ##STR264##  H    H       H                                                                                       ##STR265##  43-48                     134                                                                                ##STR266##  H    H       H                                                                                       ##STR267##  1.5406                    135                                                                                ##STR268##  H    H       H                                                                                       ##STR269##  94-97                     136                                                                                ##STR270##  H    H       H                                                                                       ##STR271##  90-92                     137                                                                                ##STR272##  H    H       H                                                                                       ##STR273##  63-69                     138                                                                                ##STR274##  H    H       H                                                                                       ##STR275##  oily solid                139                                                                                ##STR276##  H    H       H                                                                                       ##STR277##  60-63                     140                                                                                ##STR278##  H    H       H                                                                                       ##STR279##  62-64                     141                                                                                ##STR280##  H    H       H                                                                                       ##STR281##  1.5764                    142                                                                                ##STR282##  H    H       H                                                                                       ##STR283##  70-71                     143                                                                                ##STR284##  H    H       H                                                                                       ##STR285##  88-91                     144                                                                                ##STR286##  H    H       H                                                                                       ##STR287##  65-68                     145                                                                                ##STR288##  H    H       H                                                                                       ##STR289##  65-70                     146                                                                                ##STR290##  H    H       H                                                                                       ##STR291##  1.5551                    147                                                                                ##STR292##  H    H       H                                                                                       ##STR293##  dark oil                  148                                                                                ##STR294##  H    H       H                                                                                       ##STR295##  1.5582                    149                                                                                ##STR296##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR297##  1.5676                    150                                                                                ##STR298##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR299##  87-92                     151                                                                                ##STR300##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR301##  1.5835                    152                                                                                ##STR302##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR303##  90-95                     153                                                                                ##STR304##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR305##  58-65                     154                                                                                ##STR306##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR307##  55-60                     155                                                                                ##STR308##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR309##  1.6026                    156                                                                                ##STR310##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR311##  87-92                     157                                                                                ##STR312##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR313##  1.5486                    158                                                                                ##STR314##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR315##  95-98                     159                                                                                ##STR316##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR317##  1.5611                    160                                                                                ##STR318##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR319##  58-62                     161                                                                                ##STR320##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR321##  75-78                     162                                                                                ##STR322##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR323##  63-65                     163                                                                                ##STR324##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR325##  82-84                     164                                                                                ##STR326##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR327##  47-49                     165                                                                                ##STR328##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR329##  52-55                     166                                                                                ##STR330##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR331##  65-68                     167                                                                                ##STR332##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR333##  1.500                     168                                                                                ##STR334##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR335##  oily solid                169                                                                                ##STR336##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR337##  oily solid                170                                                                                ##STR338##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR339##  1.5599                    171                                                                                ##STR340##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR341##  45-50                     172                                                                                ##STR342##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR343##  80-83                     173                                                                                ##STR344##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR345##  1.5375                    174                                                                                ##STR346##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR347##  50-60                     175                                                                                ##STR348##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR349##  oily solid                176                                                                                ##STR350##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR351##  95-100                    177                                                                                ##STR352##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR353##  1.5080                    178                                                                                ##STR354##  H    CH.sub.2 CH.sub.3                                                                     H        CH.sub.2 CHOCH.sub.3                                                                       1.4858                    179                                                                                ##STR355##  H    H       H                                                                                       ##STR356##  92-93                     180                                                                                ##STR357##  CH.sub.3                                                                           CH.sub.3                                                                              H                                                                                       ##STR358##  55-60                     181                                                                                ##STR359##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR360##  1.5638                    182                                                                                ##STR361##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR362##  1.5225                    183                                                                                ##STR363##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR364##  1.5520                    184                                                                                ##STR365##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR366##  86-89                     185                                                                                ##STR367##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR368##  dark oil                  186                                                                                ##STR369##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR370##  1.5820                    187                                                                                ##STR371##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR372##  1.5451                    188                                                                                ##STR373##  H    H       H                                                                                       ##STR374##  82-84                     189                                                                                ##STR375##  H    H       H                                                                                       ##STR376##  77-78                     190                                                                                ##STR377##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR378##  68-70                     191                                                                                ##STR379##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR380##  45-49                     192                                                                                ##STR381##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR382##  1.5536                    193                                                                                ##STR383##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR384##  82.85                     194                                                                                ##STR385##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR386##  oily solid                195                                                                                ##STR387##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR388##  88-90                     196                                                                                ##STR389##  H    CH.sub.2 CH.sub.3                                                                     H                                                                                       ##STR390##  45-50                     __________________________________________________________________________

The compounds listed in the foregoing Table I were tested for herbicidalactivity by various methods and at various rates of application. Somewere tested by more than one method or at more than one rate, but atleast one method is shown for each compound to exhibit utility. Thefollowing examples are for illustrative purposes only and are notintended as necessarily representative of the overall testing performed.As one skilled in the art is aware, in herbicidal testing a significantnumber of factors that are not readily controllable can affect theresults of individual tests. For example, the results may vary dependingon environmental factors, such as amount of sunlight and water, soiltype, pH of the soil, temperature, and humidity, among other factors.Also, the depth of planting and the application rate of the herbicide,as well as the nature of crops being tested, can affect the results ofthe test. Results may vary from crop to crop and within the cropvarieties. The methods and activity are as follows:

PRE-EMERGENCE HERBICIDAL EVALUATION

Flats were filled with sandy loam soil containing a fungicide andfertilizer. The soil was leveled and rows of grassy weeds, broadleafweeds and yellow nutsedge (Cyperus esculentus), were planted thicklyenough so that several seedlings emerged per inch of row. The grassyweeds were: foxtail (Setaria viridis), watergrass (Echinochloacrus-galli) and wild oat (Avena fatua). Broadleaf weeds utilized wereannual morningglory (Ipomoea spp.) velvetleaf (Abutilon theophrasti) andmustard (Brassica kaber).

One day after planting, the flats were sprayed with a solution of a testcompound at a rate of 80 gallons of solution per acre with the compoundbeing applied at a rate of 2 lb/A (1.96 kg/ha), 4 lg/A (4.48 kg/ha), 8lb/A (8.96 kg/ha) and/or 20 lb/A (22.4 kg/ha).

Solutions of the compounds tested at 2 and 4 lb/A were made by weighingout 333 mg of the test compound into a 60 mL wide-mouth bottle anddissolving it in 25 mL of acetone containing 1% Tween® 20(polyoxyethylene sorbitan monolaurate emulsifier). Compounds tested at 8lb/A were made of solutions consisting of 480 mg of the sample tested,20 ml of acetone containing 1% Tween® 20, and 20 mL of water. Compoundstested at 20 lb/A were made of 1200 mg of test compound in 20 mL ofacetone containing 1% Tween® 20 plus 20 mL of water. Additionalsolvents, not exceeding 5 mL, were used if needed to dissolve thecompound. A 20.5 ml aliquot was taken from the stock solution anddiluted with 25 mL of an acetone:water mixture (19:1) containing 1%Tween® 20. This was used as the spray solution.

The flats were returned to the greenhouse after spraying and watereddaily by sprinkling. The degree of weed control was estimated andrecorded 3 weeks after treatment, as percentage control compared to thegrowth of the same species in an untreated check flat of the same age.

The percent control is based on the total injury to the plants due toall factors, including inhibited germination, killing of the planttissue after emergence, stunting, malformation, chlorosis, and othertypes of injury. The control ratings vary from 0 to 100 percent, where 0represents no effect with growth equal to the untreated control, and 100represents complete kill; (-) indicates the compound was not tested.

POST-EMERGENCE HERBICIDAL EVALUATION

The soil was prepared and seeded with the same varieties as describedfor the pre-emergence test. The flats were placed in the greenhouse at70°-85° F. and watered by sprinkling. Twelve to fourteen days afterplanting, the flats were sprayed at a rate of 80 gallons of solution peracre. The compound was applied at the rate of 4 lb/A (4.48 kg/ha). Thespray solution was made up similarly to that described for thepre-emergence evaluation.

The flats were returned to the greenhouse after spraying and watereddaily without wetting the foliage. Three weeks after treatment thedegree of weed control was estimated and recorded as percentage controlcompared to the growth of the same species in an untreated check flat ofthe same age. The percent control ratings were assigned on the samebasis as for the pre-emergence evaluation.

The following Table II contains the results of these tests, in terms ofaverage control of the three grasses, four broadleaf weeds, and yellownutsedge, respectively, in both pre- and post-emergence evaluations.

                  TABLE II                                                        ______________________________________                                              Rate                                                                    Cmpd. (in    Pre-Emergent    Post-Emergent                                    No.   lbs)   CYPES    AVG   AVB  CYPES  AVG   AVB                             ______________________________________                                        1     4      0        65    97   70     23    67                              2     4      0        33     0   0      0     0                               3     4      0        63    33   0      3     87                              4     4      0        88    100  0      20    67                              5     4      0        33     0   0      0     37                              6     4      70       100   100  80     98    93                              7     4      0        100   100  60     83    87                              8     4      0        37    43   0      37    37                              9     4      0        57    80   0      13    43                              10    4      0        47    83   0      0     60                              11    4      0        50    33   0      0     53                              12    4      0        0      0   0      0     0                                     8      0        37    30   0      25    3                                     20     0        37    30   0      27    3                               13    4      0        0      0   0      0     0                                     8      0        0      5   0      0     3                                     20     0        0      5   0      0     7                               14    4      75       83    100  0      83    67                              15    4      0        70    93   0      50    43                              16    4      0        0      0   0      0     7                                     8      0        0      7   0      0     20                                    20     0        7     27   0      0     25                              17    4      0        33     0   0      0     53                              18    4      0        0      0   0      0     33                              19    4      0        40    33   0      0     57                              20    4      0        0      0   0      0     0                                     8      0        3     10   0      0     32                                    20     0        3     33   0      0     45                              21    4      0        0      0   0      0     0                                     8      0        0      0   0      0     0                                     20     0        0      0   0      0     0                               22    4      0        33    47   0      0     70                              23    4      0        93    87   50     50    80                              24    4      0        0      0   0      0     40                              25    4      0        40    73   0      0     53                              26    4      0        97    100  80     87    93                              27    4      0        65    93   0      53    67                              28    4      10       83    80   20     67    73                              29    4      0        40    87   30     37    50                              30    4      0        60    68   0      20    57                              31    4      0        37    73   0      0     20                              32    4      0        68    70   0      50    57                              33    4      0        43    40   0      20    50                              34    4      0        77    60   20     27    63                              35    4      0        83    73   0      87    90                              36    4      0        100   100  30     100   100                             37    4      0        83    93   10     73    100                             38    4      0        77    83   0      50    92                              39    4      0        93    100  30     93    100                             40    4      0        73    100  0      57    100                             41    4      0        65    43   0      33    90                              42    4      0        67    57   0      53    75                              43    4      0        67    67   0      20    70                              44    4      0        70    73   0      40    93                              45    4      0        47    47   0      17    67                              46    4      0        95    100  30     90    100                             47    4      0        23    27   0      7     87                              48    4      0        23    27   0      0     63                              49    4      0        80    95   0      68    98                              50    4      0        0      0   0      0     23                              51    4      0        72    77   0      77    98                              52    4      0        57     0   0      27    0                               53    4      0        68    80   0      40    73                              54    4      0        80    82   0      57    80                              55    4      0        98    98   40     100   87                              56    4      0        78    83   0      57    90                              57    4      0        30    10   0      27    53                              58    4      20       77    100  20     60    70                              59    4      0        97    100  30     83    93                              60    4      0        87    65   0      17    82                              61    4      0        95    90   0      60    97                              62    4      0        33    40   0      17    60                              63    4      0        98    87   10     98    100                             64    4      0        68    63   0      0     75                              65    4      0        97    97   30     95    100                             66    4      0        67    50   0      40    77                              67    4      40       83    87   65     73    100                             68    4      0        98    87   0      95    100                             69    4      10       97    98   0      95    100                             70    4      0        70    62   0      33    67                              71    4      0        77    70   0      60    88                              72    4      0        53    68   0      27    40                              73    4      0        37    57   0      0     0                               74    4      0        28    33   0      40    0                               75    4      0        43    58   0      0     0                               76    4      0        78    43   0      53    47                              77    4      0        93    100  0      98    88                              78    4      0        73    67   0      43    63                              79    4      0        70    40   0      47    68                              80    4      0        100   95   0      100   100                             81    4      0        47    53   0      0     0                               82    4      0        77    82   20     70    93                              83    4      0        73    80   0      57    87                              84    4      0        23    43   0      0     0                               85    4      0        67    67   0      17    73                              86    4      0        27     7   0      0     0                               87    4      0        60    67   0      0     0                               88    4      0        100   98   0      100   100                             89    4      0        99    88   0      95    87                              90    4      0        67    67   0      17    73                              91    4      0        37     0   0      0     0                               92    4      0        80    73   0      7     90                              93    4      0        78    87   0      50    60                              94    4      30       67    90   0      20    37                              95    4      20       81    87   0      33    73                              96    4      20       83    86   30     85    57                              97    4      20       76    86   0      27    72                              98    4      0        36     7   0      0     0                               99    4      0        40     2   0      0     0                               100   4      30       87    98   10     73    88                              101   4      80       98    100  50     73    77                              102   4      0        40    28   0      0     0                               103   4      0        10    27   0      0     7                               104   4      0        0      0   0      0     0                                     8      0        0      0   0      0     0                                     20     0        0      0   0      0     0                               105   4      0        96    57   0      67    95                              106   4      0        47    57   0      63    93                              107   4      0        90    97   30     92    85                              108   4      0        93    97   30     93    83                              109   4      0        93    98   40     78    88                              110   4      0        98    98   10     95    88                              111   4      0        80    95   0      77    82                              112   4      0        97    97   0      95    75                              113   4      0        83    53   0      63    53                              114   4      10       97    98   10     100   100                             115   4      10       98    93   20     100   100                             116   4      0        73    40   0      20    40                              117   4      0        0      0   0      0     0                                     8      0        0      0   0      0     0                               118   4      0        37    33   0      0     0                               119   4      0        0      0   0      0     0                                     8      0        37    48   0      12    37                              120   4      0        0      0   0      0     0                                     8      0        0      0   0      10    30                              121   4      0        100   93   0      87    100                             122   4      0        100   97   0      80    100                             123   4      0        47    73   0      17    53                              124   4      0        80    100  0      78    93                              125   4      0        73    47   0      0     0                               126   4      0        73    47   30     10    43                              127   4      0        77    93   20     68    87                              128   4      20       70    77   60     40    60                              129   4      0        100   95   60     43    50                              130   4      30       93    100  70     63    97                              131   4      0        33     0   0      0     0                               132   4      0        100   100  10     83    80                              133   4      0        93    43   0      7     40                              134   4      0        67    40   0      0     0                               135   4      0        67    43   0      0     37                              136   4      0        77    95   0      60    67                              137   4      70       95    100  80     87    87                              138   4      0        80    100  20     70    77                              139   4      0        67    47   20     43    57                              140   4      20       73    80   30     50    77                              141   4      0        73    40   0      7     40                              142   4      0        100   93   30     73    67                              143   4      30       70    82   80     53    63                              144   4      50       97    93   30     67    83                              145   4      60       73    67   70     67    60                              146   4      0        97    73   0      63    97                              147   4      0        100   93   0      83    87                              148   4      0        98    77   0      53    100                             149   4      0        65    80   0      67    60                              150   4      0        33    33   0      7     57                              151   4      30       100   100  30     90    87                              152   4      0        93    73   0      40    93                              153   4      0        70    67   0      43    97                              154   4      30       80    87   30     80    92                              155   4      0        93    57   0      13    70                              156   4      30       100   37   0      30    67                              157   4      0        43    33   0      10    67                              158   4      0        50    40   0      20    47                              159   4      0        97    93   0      70    73                              160   4      30       73    93   30     40    53                              161   4      0        67    87   0      62    60                              162   4      0        60    50   0      30    60                              163   4      30       70    80   30     67    87                              164   4      0        47    37   0      23    60                              165   4      0        77    93   0      77    85                              166   2      0        40    40   0      3     7                               167   2      0        87    100  0      53    80                              168   2      10       67    67   20     50    73                              169   2      0        70    53   0      23    53                              170   2      0        33    27   0      3     17                              171   2      0        67    47   0      17    70                              172   2      0        93    100  0      67    93                              173   2      0        0      0   0      0     0                               174   2      0        90    97   30     93    87                              175   2      30       100   100  50     97    90                              176   2      0        43    53   0      0     0                               177   2      0        13    20   0      0     33                              178   2      70       87    87   20     47    77                              179   2      20       88    80   40     43    67                              180   2      0        0      0   0      0     0                               181   2      80       98    73   0      47    47                              182   2      0        97    92   0      82    53                              183   2      0        100   100  0      27    30                              184   2      0        98    93   0      60    43                              185   2      0        98    75   0      0     37                              186   2      0        23    10   0      0     47                              187   2      0        93    50   0      30    53                              188   2      0        0      0   0      0     0                               189   2      0        0      0   0      0     0                               190   2      40       98    100  60     85    88                              191   2      0        40    23   0      0     0                               192   2      0        70    57   0      47    73                              193   2      0        68    40   0      30    53                              194   2      0        73    53   0      57    60                              195   2      0        40    28   0      0     37                              196   2      40       73    70   60     77    57                              ______________________________________                                         PG,35

Although Compound No. 104 showed no apparent activity in our 2 lb and 4lb screens above, it did exhibit some activity in our controlled lightpost-emergence screen described below. Following is a table of itsactivity.

CONTROLLED LIGHT POST-EMERGENCE MULTI-WEED/MULTI-CROP EVALUATION

The soil was prepared and seeded as described for the pre-emergencetest. Flats containing seeds of broadleaf species were placed in thegreenhouse 21 days, and flats containing seeds of grass species wereplaced in the greenhouse 14 days before spraying at the same rates as inthe pre-emergence evaluation.

After spraying, the flats were returned to the greenhouse and watereddaily. Three to four weeks after treatment, the degree of control wasestimated and the percent control ratings were assigned on the samebasis as for the pre-emergence evaluation.

The following Table III contains the results of these tests in terms ofaverage control of the four grasses, five broadleaf weeds and threecrops in these evaluations.

                  TABLE III                                                       ______________________________________                                        Post-Emergence                                                                Cmpd. Rate   Average  Average Sugar-                                          No.   lb/A   Grasses  Broadleaf                                                                             beet   Barley                                                                              Wheat                              ______________________________________                                        104   4      0        24      30     0     0                                  ______________________________________                                    

The compounds of the present invention are useful as herbicides and canbe applied in a variety of ways known to those skilled in the art, atvarious concentrations. In practice, the compounds are applied asformulations containing the various adjuvants and carriers known to orused in the industry for facilitating dispersion. The choice offormulation and mode of application for any given compound may affectits activity, and selection will be made accordingly. The compounds ofthe invention may thus be formulated as granules, as wettable powders,as emulsifiable concentrates, as powders or dusts, as flowables, assolutions, suspensions or emulsions, or in controlled-release forms suchas microcapsules. These formulations may contain as little as about 0.5%to as much as about 95% or more by weight of active ingredient. Theoptimum amount for any given compound will depend upon the nature of theseeds or plants to be controlled. The rate of application will generallyvary from about 0.01 to about 10 pounds per acre, preferably from about0.02 to about 4 pounds per acre.

Wettable powders are finely divided particles which disperse readily inwater or other liquid carriers. The particles contain the activeingredient retained in a solid matrix. Typical solid matrices includefuller's earth, kaolin clays, silicas and other readily wet organic orinorganic solids. Wettable powders normally contain about 5% to about95% of the active ingredient plus a small amount of wetting, dispersingor emulsifying agents.

Emulsifiable concentrates are homogeneous liquid compositionsdispersible in water or other liquid, and may consist entirely of theactive compound with a liquid or solid emulsifying agent, or may alsocontain a liquid carrier, such as xylene, heavy aromatic naphthas,isophorone and other non-volatile organic solvents. In use, theseconcentrates are dispersed in water or other liquid and normally appliedas a spray to the area to be treated. The amount of active ingredientmay range from about 0.5% to about 95% of the concentrate.

Granular formulations include both extrudates and relatively coarseparticles, and are usually applied without dilution to the area in whichsuppression of vegetation is desired. Typical carriers for granularformulations include sand, fuller's earth, attapulgite clay, bentoniteclays, montmorillonite clay, vermiculite, perlite and other organic orinorganic materials which absorb or which can be coated with the activecompound. Granular formulations normally contain about 5% to about 25%active ingredients which may include surface-active agents such as heavyaromatic naphthas, kerosene or other petroleum fractions, or vegetableoils; and/or stickers such as dextrins, glue or synthetic resins.

Dusts are free-flowing admixtures of the active ingredient with finelydivided solids such as talc, clays, flours and other organic andinorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the active materialenclosed in an inert porous shell which allows escape of the enclosedmaterial to the surroundings at controlled rates. Encapsulated dropletsare typically about 1 to 50 microns in diameter. The enclosed liquidtypically constitutes about 50 to 95% of the weight of the capsule, andmay include solvent in addition to the active compound. Encapsulatedgranules are generally porous granules with porous membranes sealing thegranule pore openings, retaining the active species in liquid forminside the granule pores. Granules typically range from 1 millimeter to1 centimeter, preferably 1 to 2 millimeters in diameter. Granules areformed by extrusion, agglomeration or prilling, or are naturallyoccurring. Examples of such materials are vermiculite, sintered clay,kaolin, attapulgite clay, sawdust and granular carbon. Shell or membranematerials include natural and synthetic rubbers, cellulosic materials,styrene-butadiene copolymers, polyacrylonitriles, polyecrylates,polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other useful formulations for herbicidal applications include simplesolutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene and other organic solvents. Pressurizedsprays, wherein the active ingredient is dispersed in finely-dividedform as a result of vaporization of a low boiling dispersant solventcarrier, such as the Freons, may also be used.

Many of these formulations include wetting, dispersing or emulsifyingagents. Examples are alkyl and alkylaryl sulfonates and sulfates andtheir salts; polyhydric alcohols; polyethoxylated alcohols; esters andfatty amines. These agents when used normally comprise from 0.1% to 15%by weight of the formulations.

The compounds of the present invention are also useful when combinedwith other herbicides and/or defoliants, dessicants, growth inhibitors,and the like. These other materials can comprise from about 5% to about95% of the active ingredients in the formulations. These combinationsfrequently provide a higher level of effectiveness in controlling weedsand often provide results unattainable with separate formulations of theindividual herbicides.

Examples of other herbicides, defoliants, dessicants and plant growthinhibitors with which the compounds of this invention can be combinedare:

chlorophenoxy herbicides such as 2,4-D, 2,4,5-T, MCPA, MCPB, 2,4-DB,2,4-DEB, 4-CPA, 2,4,5-TB and silvex;

carbamate herbicides such as propham, chlorpropham, swep and barban;

thiocarbamate and dithiocarbamate herbicides such as CDEC,metham-sodium, EPTC, diallate, PEBC and vernolate;

substituted urea herbicides such as norea, dichloral urea, chloroxuron,cycluron, fenuron, monuron, monuron TCA, diuron, linuron, monolinuronneburon, buturon and trimeturon;

symmetrical triazine herbicides such as simazine, chlorazine,desmetryne, norazine, ipazine, prometryn, atrazine, trietazine,simetone, prometone, propazine and ametryne;

chlorinated aliphatic acid herbicides such as TCA and dalapon;

chlorinated benzoic acid and phenylacetic acid herbicides such as2,3,6-TBA, dicamba, tricamba, chloramben, fenac, PBA,2-methoxy-3,6-dichlorophenylacetic acid,3-methoxy-2,6-dichlorophenylacetic acid,2-methoxy-3,5,6-trichlorophenylacetic acid and2,4-dichloro-3-nitrobenzoic acid;

and such compounds as aminotriazole, maleic hydrazide, phenylmercuryacetate, endothal, technical chlordane, DCPA, diquat, erbon, DNC, DNBP,dichlobenil, DPA, diphenamide, dipropalin, trifluralin, solan, dicryl,merphos, DMPA, DSMA, MSMA, potassium azide, acrolein, benefin,bensulide, AMS, bromacil,2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxazolidine-3,5-dione, bromoxynil,cacodylic acid, CMA, CPMF, cypromid, DCB, DCPA, dichlone, diphenatril,DMTT, DNAP, EBEP, EXD, HCA, ioxynil, IPX, isocil, potassium cyanate,MAA, MAMA, MCPES, MCPP, MH, molinate, NPA, OCH, paraquat, PCP, picloram,DPA, PCA, sesone, terbacil, terbutol, TCBA, alachlor, nitralin, sodiumtetraborate, calcium cyanamide, S,S,S-tributylphosphorotrithioate andpropanil.

These formulations can be applied to the areas where control is desiredby conventional methods. Dust and liquid compositions, for example, canbe applied by the use of power-dusters, boom and hand sprayers and spraydusters. The formulations can also be applied from airplanes as a dustor a spray or by rope wick applications. To modify or control growth ofgerminating seeds or emerging seedlings, dust and liquid formulationscan be distributed in the soil to a depth of at least one-half inchbelow the soil surface or applied to the soil surface only, by sprayingor sprinkling. The formulations can also be applied by addition toirrigation water. This permits penetration of the formulations into thesoil together with the irrigation water. Dust compositions, granularcompositions or liquid formualtions applied to the surface of the soilcan be distributed below the surface of the soil by conventional meanssuch as discing, dragging or mixing operations.

The following are examples of typical formulations.

5% dust:

5 parts active compound

95 parts talc

2% dust:

2 parts active compound

1 part highly dispersed silicic acid

97 parts talc

These dusts are formed by mixing the components then grinding themixture to the desired particle size.

5% granules:

5 parts active compound

0.25 part epichlorohydrin

0.25 part cetyl polyglycol ether

3.5 parts polyethylene glycol

91 parts kaolin (particle size 0.3-0.8 mm)

Granules are formed by mixing the active compound with epichlorohydrinand dissolving the mixture in 6 parts of acetone. The polyethyleneglycol and cetyl polyglycol ether are then added. The resultant solutionis sprayed on the kaolin and the acetone evaporated in vacuo.

    ______________________________________                                        wettable powders                                                              ______________________________________                                        70%  70 parts active compound                                                      5 parts sodium dibutylnaphthylsulfonate                                       3 parts naphthalenesulfonic acid/phenolsulfonic                               acid/formaldehyde condensate (3:2:1)                                          10 parts kaolin                                                               12 parts Champagne chalk                                                 40%  40 parts active compound                                                      5 parts sodium lignin sulfonate                                               1 part sodium dibutylnaphthalenesulfonic acid                                 54 parts silicic acid                                                    25%  25 parts active compound                                                      4.5 parts calcium lignin sulfate                                              1.9 parts Champagne chalk/hydroxyethyl cellulose (1:1)                        1.5 parts sodium dibutylnaphthalenesulfonate                                  19.5 parts silicic acid                                                       19.5 parts Champagne chalk                                                    28.1 parts kaolin                                                        25%  25 parts active compound                                                      2.5 parts isooctylphenoxy-polyethylene-ethanol                                1.7 parts Champagne chalk/hydroxyethyl cellulose (1:1)                        8.3 parts sodium aluminum silicate                                            16.5 parts kieselguhr                                                         46 parts kaolin                                                          10%  10 parts active compound                                                      3 parts of a mixture of sodium salts of saturated                             fatty alcohol sulfates                                                        5 parts of naphthalenesulfonic acid/formaldehyde                              condensate                                                                    82 parts kaolin                                                          ______________________________________                                    

These wettable powders are prepared by intimately mixing the activecompounds with the additives in suitable mixers, and grindig theresulting mixtures in mills or rollers.

25% emulsifiable concentrate:

25 parts active substance

2.5 parts epoxidized vegetable oil

10 parts of an alkylarylsulfonate/fatty alcohol polyglycol ether mixture

5 parts dimethylformamide

57.5 parts xylene

What is claimed is:
 1. A compound having the formula ##STR391## whereinR is phenyl, or phenyl substituted with one or more C₁ -C₃ lower alkyl,C₁ -C₃ lower alkoxy, halo, C₁ -C₃ lower haloalkyl, cyano, nitro,phenoxy, C₁ -C₃ lower alkylsulfonyl or combinations thereof;R₁ ishydrogen or C₁ -C₃ lower alkyl; R₂ is selected from the group consistingof hydrogen, C₁ -C₃ lower alkyl, C₃ -C₆ cycloalkyl and C₁ -C₃ loweralkylalkoxy; R₃ is selected from the group consisting of hydrogen; C₁-C₆ lower alkyl; C₂ -C₆ lower alkenyl; C₂ -C₆ lower alkynyl; phenyl orphenyl substituted with one or more C₁ -C₃ lower alkyl, C₁ -C₃ loweralkoxy, halo, C₁ -C₃ lower haloalkyl, nitro, C₁ -C₃ lower alkylthio, C₁-C₃ lower alkylsulfonyl or combinations thereof; benzyl, alpha-alkylsubstituted benzyl, or benzyl substituted with one or more C₁ -C₃ loweralkyl, halo, C₁ -C₃ lower haloalkyl, or combinations thereof; R₄ isselected from the group consisting of hydrogen; C₁ -C₆ lower alkyl; C₂-C₆ lower alkenyl; C₂ -C₆ lower alkynyl; phenyl or phenyl substitutedwith one or more C₁ -C₃ lower alkyl, C₁ -C₃ lower alkoxy, halo, C₁ -C₃lower haloalkyl, nitro, C₁ -C₃ lower alkylthio, C₁ -C₃ loweralkylsulfonyl or combinations thereof; benzyl, alpha-alkyl substitutedbenzyl, or benzyl substituted with one or more C₁ -C₃ lower alkyl, halo,C₁ -C₃ lower haloalkyl, or combinations thereof; provided that when R₃is hydrogen or C₁ -C₆ lower alkyl, R₄ is not hydrogen or C₁ -C₆ loweralkyl.
 2. A compound according to claim 1 wherein R is phenyl or phenylsubstituted with one or more fluorine, chlorine, bromine, iodine ortrifluoromethyl; R₁ is hydrogen or methyl; R₂ is methyl methoxy orethyl; R₃ is hydrogen or ethyl; and R₄ is phenyl or phenyl substitutedwith one or more methyl, fluorine, chlorine, bromine, iodine ortrifluoromethyl or benzyl or benzyl substituted with one or morefluorine, chlorine, bromine, iodine or trifluoromethyl.
 3. A compoundaccording to claim 2 wherein R₁ is hydrogen, R₂ is ethyl, and R₃ ishydrogen.
 4. A compound according to claim 3 wherein R istrifluoromethylphenyl or chlorophenyl and R₄ is methylbenzyl,chlorobenzyl or trifluoromethylbenzyl.
 5. A compound according to claim4 wherein R is substituted meta and R₄ is substituted ortho.
 6. Acompound according to claim 5 wherein R is meta-trifluoromethylphenyl.7. A compound according to claim 6 wherein R₄ is ortho-chlorobenzyl. 8.A compound according to claim 6 wherein R₄ is ortho-methylbenzyl.
 9. Acompound according to claim 6 wherein R₄ is ortho-trifluoromethylbenzyl.10. A compound according to claim 5 wherein R is meta-chlorophenyl. 11.A compound according to claim 10 wherein R₄ isortho-trifluoromethylbenzyl.
 12. An herbicidal compositioncomprising:(a) an herbicidally effective amount of a compound having theformula ##STR392## wherein R is phenyl, or phenyl substituted with oneor more C₁ -C₃ lower alkyl, C₁ -C₃ lower alkoxy, halo, C₁ -C₃ lowerhaloalkyl, cyano, nitro, phenoxy, C₁ -C₃ lower alkylsulfonyl orcombinations thereof; R₁ is hydrogen or C₁ -C₃ lower alkyl; R₂ isselected from the group consisting of hydrogen, C₁ -C₃ lower alkyl, C₃-C₆ cycloalkyl and C₁ -C₃ lower alkylalkoxy; R₃ is selected from thegroup consisting of hydrogen; C₁ -C₆ lower alkyl; C₂ -C₆ lower alkenyl;C₂ -C₆ lower alkynyl; phenyl or phenyl substituted with one or more C₁-C₃ lower alkyl, C₁ -C₃ lower alkoxy, halo, C₁ -C₃ lower haloalkyl,nitro, C₁ -C₃ lower alkylthio, C₁ -C₃ lower alkylsulfonyl orcombinations thereof; benzyl, alpha-alkyl substituted benzyl, or benzylsubstituted with one or more C₁ -C₃ lower alkyl, halo, C₁ -C₃ lowerhaloalkyl, or combinations thereof;R₄ is selected from the groupconsisting of hydrogen; C₁ -C₆ lower alkyl; C₂ -C₆ lower alkenyl; C₂ -C₆lower alkynyl; phenyl or phenyl substituted with one or more C₁ -C₃lower alkyl, C₁ -C₃ lower alkoxy, halo, C₁ -C₃ lower haloalkyl, nitro,C₁ -C₃ lower alkylthio, C₁ -C₃ lower alkylsulfonyl or combinationsthereof; benzyl, alpha-alkyl substituted benzyl, or benzyl substitutedwith one or more C₁ -C₃ lower alkyl, halo, C₁ -C₃ lower haloalkyl, orcombinations thereof; provided that when R₃ is hydrogen or C₁ -C₆ loweralkyl, R₄ is not hydrogen or C₁ -C₆ lower alkyl; and (b) an inertdiluent carrier therefor.
 13. An herbicidal composition according toclaim 12 wherein R is phenyl or phenyl substituted with one or morefluorine, chlorine, bromine, iodine or trifluoromethyl; R₁ is hydrogenor methyl; R₂ is methyl methoxy or ethyl; R₃ is hydrogen or ethyl; andR₄ is phenyl or phenyl substituted with one or more methyl, fluorine,chlorine, bromine, iodine or trifluoromethyl or benzyl or benzylsubstituted with one or more fluorine, chlorine, bromine, iodine ortrifluoromethyl.
 14. An herbicidal composition according to claim 13wherein R₁ is hydrogen, R₂ is ethyl, and R₃ is hydrogen.
 15. Anherbicidal composition according to claim 14 wherein R istrifluoromethylphenyl or chlorophenyl and R₄ is methylbenzyl,chlorobenzyl or trifluoromethylbenzyl.
 16. An herbicidal compositionaccording to claim 15 wherein R is substituted meta and R₄ issubstituted ortho.
 17. An herbicidal composition according to claim 16wherein R is meta-trifluoromethylphenyl.
 18. An herbicidal compositionaccording to claim 17 wherein R₄ is ortho-chlorobenzyl.
 19. Anherbicidal composition according to claim 17 wherein R₄ isortho-methylbenzyl.
 20. An herbicidal composition according to claim 17wherein R₄ is ortho-trifluoromethylbenzyl.
 21. An herbicidal compositionaccording to claim 16 wherein R is meta-chlorophenyl.
 22. An herbicidalcomposition according to claim 21 wherein R₄ isortho-trifluoromethylbenzyl.
 23. A method of controlling undesirablevegetation comprising applying to said vegetation or to the locusthereof, an herbicidally effective amount of a compound having theformula ##STR393## wherein R is phenyl, or phenyl substituted with oneor more C₁ -C₃ lower alkyl, C₁ -C₃ lower alkoxy, halo, C₁ -C₃ lowerhaloalkyl, cyano, nitro, phenoxy, C₁ -C₃ lower alkylsulfonyl orcombinations thereof;R₁ is hydrogen or C₁ -C₃ lower alkyl; R₂ isselected from the group consisting of hydrogen, C₁ -C₃ lower alkyl, C₃-C₆ cycloalkyl, C₁ -C₃ lower alkylalkoxy or combinations thereof; R₃ isselected from the group consisting of hydrogen; C₁ -C₆ lower alkyl; C₂-C₆ lower alkenyl; C₂ -C₆ lower alkynyl; phenyl or phenyl substitutedwith one or more halogen or C₁ -C₃ lower alkyl; substituted with one ormore C₁ -C₃ lower alkyl, C₁ -C₃ lower alkoxy, halo, C₁ -C₃ lowerhaloalkyl, nitro, C₁ -C₃ lower alkylthio, C₁ -C₃ lower alkylsulfonyl orcombinations thereof; benzyl, alpha-alkyl substituted benzyl, or benzylsubstituted with one or more C₁ -C₃ lower alkyl, halo, C₁ -C₃ lowerhaloalkyl, or combinations thereof; R₄ is selected from the groupconsisting of hydrogen; C₁ -C₆ lower alkyl; C₂ -C₆ lower alkenyl; C₂ -C₆lower alkynyl; phenyl or phenyl substituted with one or more C₁ -C₃lower alkyl, C₁ -C₃ lower alkoxy, halo, C₁ -C₃ lower haloalkyl, nitro,C₁ -C₃ lower alkylthio, C₁ -C₃ lower alkylsulfonyl or combinationsthereof; benzyl, alpha-alkyl substituted benzyl, or benzyl substitutedwith one or more C₁ -C₃ lower alkyl, halo, C₁ -C₃ lower haloalkyl, orcombinations thereof; provided that when R₃ is hydrogen or C₁ -C₆ loweralkyl, R₄ is not hydrogen or C₁ -C₆ lower alkyl.
 24. A method accordingto claim 23 wherein R is phenyl or phenyl substituted with one or morefluorine, chlorine, bromine, iodine or trifluoromethyl; R₁ is hydrogenor methyl; R₂ is methyl methoxy or ethyl; R₃ is hydrogen or ethyl; andR₄ is phenyl or phenyl substituted with one or more methyl, fluorine,chlorine, bromine, iodine or trifluoromethyl or benzyl or benzylsubstituted with one or more fluorine, chlorine, bromine, iodine ortrifluoromethyl.
 25. The method according to claim 24 wherein R₁ ishydrogen, R₂ is ethyl, and R₃ is hydrogen.
 26. The method according toclaim 25 wherein R is trifluoromethylphenyl or chlorophenyl and R₄ ismethylbenzyl, chlorobenzyl or trifluoromethylbenzyl.
 27. The methodaccording to claim 26 wherein R is substituted meta and R₄ issubstituted ortho.
 28. The method according to claim 27 wherein R ismeta-trifluoromethylphenyl.
 29. The method according to claim 28 whereinR₄ is ortho-chlorobenzyl.
 30. The method according to claim 28 whereinR₄ is ortho-methylbenzyl.
 31. The method according to claim 28 whereinR₄ is ortho-trifluoromethylbenzyl.
 32. The method according to claim 27wherein R is meta-chlorophenyl.
 33. The method according to claim 30wherein R₄ is ortho-trifluoromethylbenzyl.